Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes

被引:248
作者
de Nanteuil, F. [1 ]
De Simone, F. [1 ]
Frei, R. [1 ]
Benfatti, F. [1 ]
Serrano, E. [1 ]
Waser, J. [1 ]
机构
[1] Ecole Polytech Fed Lausanne, ISIC, LCSO, SB, CH-1015 Lausanne, Switzerland
基金
瑞士国家科学基金会;
关键词
DONOR-ACCEPTOR CYCLOPROPANES; FORMAL 4+2 CYCLOADDITION; ASYMMETRIC 3+2 CYCLOADDITION; ALPHA-AMINO-ACIDS; ORGANIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; RING-ENLARGEMENT; N-CYCLOPROPYLIMINE-1-PYRROLINE PHOTOREARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; ACTIVATED CYCLOPROPANES;
D O I
10.1039/c4cc03194f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cyclization and annulation reactions initiated by ring-opening of small rings, especially cyclopropanes and cyclobutanes are now well-established in synthetic chemistry. Nevertheless, the potential of aminocyclopropanes and cyclobutanes, an important subclass for the synthesis of nitrogen-rich building blocks, has remained unexploited for a long time, despite important pioneering results. In the last decade, the situation has changed dramatically and new catalytic methods have emerged both for cyclization and annulation reactions. The purpose of this feature article is to present recent progress in this area, including our own work using donor-acceptor cyclopropanes and cyclobutanes.
引用
收藏
页码:10912 / 10928
页数:17
相关论文
共 130 条
  • [1] Preparation and intramolecular [2+2]-photocycloaddition of 1,5-dihydropyrrol-2-ones and 5,6-dihydro-1H-pyridin-2-ones with C-, N-, and O-linked alkenyl side chains at the 4-position
    Albrecht, Dominik
    Basler, Birte
    Bach, Thorsten
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06) : 2345 - 2356
  • [2] Asymmetric Organocatalytic Formal [2+2]-Cycloadditions via Bifunctional H-Bond Directing Dienamine Catalysis
    Albrecht, Lukasz
    Dickmeiss, Gustav
    Acosta, Fabio Cruz
    Rodriguez-Escrich, Carles
    Davis, Rebecca L.
    Jorgensen, Karl Anker
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) : 2543 - 2546
  • [3] Preparation of highly substituted tetrahydropyrans via a metal assisted dipolar cycloaddition reaction
    Allart, Eric A.
    Christie, Steven D. R.
    Pritchard, Gareth J.
    Elsegood, Mark R. J.
    [J]. CHEMICAL COMMUNICATIONS, 2009, (47) : 7339 - 7341
  • [4] Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.0.CO
  • [5] 2-E
  • [6] Selective Michael Aldol reaction by use of sterically hindered aluminum aryloxides as Lewis acids: An easy approach to cyclobutane amino acids
    Avenoza, A
    Busto, JH
    Canal, N
    Peregrina, JM
    Pérez-Fernández, M
    [J]. ORGANIC LETTERS, 2005, 7 (16) : 3597 - 3600
  • [7] C-2/C-3 annulation and C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters
    Bajtos, Barbora
    Yu, Ming
    Zhao, Hongda
    Pagenkopf, Brian L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (31) : 9631 - 9634
  • [8] Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones
    Benfatti, Fides
    de Nanteuil, Florian
    Waser, Jerome
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (16) : 4844 - 4849
  • [9] Iron-Catalyzed [3+2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans
    Benfatti, Fides
    de Nanteuil, Florian
    Waser, Jerome
    [J]. ORGANIC LETTERS, 2012, 14 (01) : 386 - 389
  • [10] Natural occurrence, syntheses, and applications of cyclopropyl-group-containing α-amino acids.: 2.: 3,4- and 4,5-methanoamino acids
    Brackmann, Farina
    de Meijere, Armin
    [J]. CHEMICAL REVIEWS, 2007, 107 (11) : 4538 - 4583